CA2418008C - Antifungal ketoconazole composition for topical use - Google Patents

Antifungal ketoconazole composition for topical use Download PDF

Info

Publication number: CA2418008C
Authority: CA; Canada
Prior art keywords: ketoconazole; amount; present; water; alcohol
Prior art date: 2000-08-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002418008A

Other languages

English (en)

French (fr)

Other versions

CA2418008A1 (en

Inventor

Martin Whitefield

Andrew James Dixon

Susan Colette Temple

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Diomed Developments Ltd

Original Assignee

Diomed Developments Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-08-18

Filing date

2001-08-14

Publication date

2009-11-03

2001-08-14 Application filed by Diomed Developments Ltd filed Critical Diomed Developments Ltd

2002-02-28 Publication of CA2418008A1 publication Critical patent/CA2418008A1/en

2009-11-03 Application granted granted Critical

2009-11-03 Publication of CA2418008C publication Critical patent/CA2418008C/en

2021-08-14 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229960004125 ketoconazole Drugs 0.000 title claims abstract description 55
230000000699 topical effect Effects 0.000 title claims abstract description 11
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 title claims abstract 8
239000000203 mixture Substances 0.000 title claims description 52
230000000843 anti-fungal effect Effects 0.000 title description 3
229940121375 antifungal agent Drugs 0.000 title description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
239000004094 surface-active agent Substances 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
238000009835 boiling Methods 0.000 claims abstract description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
229940074047 glyceryl cocoate Drugs 0.000 claims description 9
125000003976 glyceryl group Polymers [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 9
239000003246 corticosteroid Substances 0.000 claims description 6
206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 5
208000008742 seborrheic dermatitis Diseases 0.000 claims description 5
206010012504 Dermatophytosis Diseases 0.000 claims description 4
241001460074 Microsporum distortum Species 0.000 claims description 4
208000010195 Onychomycosis Diseases 0.000 claims description 4
241000101040 Pityriasis Species 0.000 claims description 4
208000002474 Tinea Diseases 0.000 claims description 4
208000007712 Tinea Versicolor Diseases 0.000 claims description 4
206010043866 Tinea capitis Diseases 0.000 claims description 4
206010056131 Tinea versicolour Diseases 0.000 claims description 4
201000003984 candidiasis Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
201000000508 pityriasis versicolor Diseases 0.000 claims description 4
201000005882 tinea unguium Diseases 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
XMAYWYJOQHXEEK-ZEQKJWHPSA-N (2S,4R)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@H]1O[C@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-ZEQKJWHPSA-N 0.000 description 48
210000003491 skin Anatomy 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
210000004761 scalp Anatomy 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000000243 solution Substances 0.000 description 12
239000006071 cream Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000002453 shampoo Substances 0.000 description 7
-1 ketoconazole compound Chemical class 0.000 description 6
210000000434 stratum corneum Anatomy 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
150000002460 imidazoles Chemical class 0.000 description 4
238000000034 method Methods 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
238000009792 diffusion process Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000008213 purified water Substances 0.000 description 3
244000060011 Cocos nucifera Species 0.000 description 2
235000013162 Cocos nucifera Nutrition 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229960001102 betamethasone dipropionate Drugs 0.000 description 2
CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000012458 free base Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
229940064438 nizoral Drugs 0.000 description 2
239000003002 pH adjusting agent Substances 0.000 description 2
239000012466 permeate Substances 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
239000003760 tallow Substances 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
229920001651 Cyanoacrylate Polymers 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
241000555688 Malassezia furfur Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
229960004022 clotrimazole Drugs 0.000 description 1
229940071160 cocoate Drugs 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
238000002224 dissection Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000002314 glycerols Polymers 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000001165 hydrophobic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000001524 infective effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940043348 myristyl alcohol Drugs 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000003260 vortexing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cosmetics (AREA)

CA002418008A 2000-08-18 2001-08-14 Antifungal ketoconazole composition for topical use Expired - Fee Related CA2418008C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0020486A GB2365770B (en)	2000-08-18	2000-08-18	Antifungal ketoconazole composition for topical use
GB0020486.7		2000-08-18
PCT/GB2001/003634 WO2002015936A1 (en)	2000-08-18	2001-08-14	Antifungal ketoconazole composition for topical use

Publications (2)

Publication Number	Publication Date
CA2418008A1 CA2418008A1 (en)	2002-02-28
CA2418008C true CA2418008C (en)	2009-11-03

Family

ID=9897945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002418008A Expired - Fee Related CA2418008C (en)	2000-08-18	2001-08-14	Antifungal ketoconazole composition for topical use

Country Status (13)

Country	Link
US (1)	US7732450B2 (de)
EP (1)	EP1309352B1 (de)
AT (1)	ATE266421T1 (de)
AU (2)	AU7656701A (de)
CA (1)	CA2418008C (de)
DE (1)	DE60103284T2 (de)
DK (1)	DK1309352T3 (de)
ES (1)	ES2220787T3 (de)
GB (1)	GB2365770B (de)
IL (2)	IL153592A0 (de)
PT (1)	PT1309352E (de)
WO (1)	WO2002015936A1 (de)
ZA (1)	ZA200210076B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6846837B2 (en)	2002-06-21	2005-01-25	Howard I. Maibach	Topical administration of basic antifungal compositions to treat fungal infections of the nails
US9211286B2 (en) *	2006-09-12	2015-12-15	Curatek Pharmaceuticals Holding, Inc.	Terconazole composition and method
FR2912917B1 (fr) *	2007-02-26	2012-05-18	Oreal	Milieu conditionne et ses utilisations
US20090062244A1 (en) *	2007-09-04	2009-03-05	Joseph Schwarz	Pharmaceutical composition
EP2651450B1 (de) *	2010-12-16	2015-12-16	Borje S. Andersson	Pharmazeutische azolformulierungen zur parenteralen verabreichung und verfahren zu ihrer herstellung und anwendung bei der behandlung von gegenüber azolverbindungen sensiblen erkrankungen
HUE034480T2 (en)	2011-04-28	2018-02-28	Platform Brightworks Two Ltd	Improved parenteral formulations of lipophilic pharmaceutical agents and methods for preparing and using the same
BR112013033239A2 (pt)	2011-06-22	2016-09-06	Vyome Biosciences	pró-farmácos de conjugado baseado em atifungicos e antibacterianos
MX2015016675A (es)	2013-06-04	2016-07-15	Vyome Biosciences Pvt Ltd	Particulas recubiertas y composiciones que comprenden las mismas.
WO2021030174A1 (en) *	2019-08-09	2021-02-18	University Of Connecticut	Truncated itraconazole analogues and methods of use thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5641475A (en) *	1987-05-15	1997-06-24	Tristrata, Inc.	Antiodor, antimicrobial and preservative compositions and methods of using same
GB8910069D0 (en) *	1989-05-03	1989-06-21	Janssen Pharmaceutica Nv	Method of topically treating acne vulgaris
US5100908A (en) *	1990-03-06	1992-03-31	Ss Pharmaceutical Co., Ltd.	Antimycotic external imidazole preparations
ES2098921T3 (es) *	1993-01-21	1997-05-01	Janssen Pharmaceutica Nv	Composiciones de cetoconazol de uso topico.
US5461068A (en) *	1993-09-29	1995-10-24	Corwood Laboratories, Inc.	Imidazole derivative tincture and method of manufacture
TW449485B (en) *	1995-03-31	2001-08-11	Colgate Palmolive Co	Skin care products containing anti itching/anti irritant agents
US6159479A (en) *	1997-09-16	2000-12-12	L'oreal	Hydrous salicylic acid solutions
AUPO983897A0 (en) *	1997-10-17	1997-11-06	Soltec Research Pty Ltd	Topical antifungal composition

2000
- 2000-08-18 GB GB0020486A patent/GB2365770B/en not_active Expired - Fee Related
2001
- 2001-08-14 AU AU7656701A patent/AU7656701A/xx active Pending
- 2001-08-14 DE DE60103284T patent/DE60103284T2/de not_active Expired - Lifetime
- 2001-08-14 ES ES01954225T patent/ES2220787T3/es not_active Expired - Lifetime
- 2001-08-14 PT PT01954225T patent/PT1309352E/pt unknown
- 2001-08-14 IL IL15359201A patent/IL153592A0/xx not_active IP Right Cessation
- 2001-08-14 AT AT01954225T patent/ATE266421T1/de active
- 2001-08-14 DK DK01954225T patent/DK1309352T3/da active
- 2001-08-14 EP EP01954225A patent/EP1309352B1/de not_active Expired - Lifetime
- 2001-08-14 CA CA002418008A patent/CA2418008C/en not_active Expired - Fee Related
- 2001-08-14 WO PCT/GB2001/003634 patent/WO2002015936A1/en not_active Ceased
- 2001-08-14 US US10/343,984 patent/US7732450B2/en not_active Expired - Fee Related
- 2001-08-14 AU AU2001276567A patent/AU2001276567B2/en not_active Ceased
2002
- 2002-12-12 ZA ZA200210076A patent/ZA200210076B/en unknown
- 2002-12-23 IL IL153592A patent/IL153592A/en unknown

Also Published As

Publication number	Publication date
ES2220787T3 (es)	2004-12-16
GB2365770A (en)	2002-02-27
EP1309352B1 (de)	2004-05-12
DE60103284T2 (de)	2005-05-19
CA2418008A1 (en)	2002-02-28
AU7656701A (en)	2002-03-04
IL153592A (en)	2008-04-13
WO2002015936A1 (en)	2002-02-28
DK1309352T3 (da)	2004-08-30
ZA200210076B (en)	2003-10-16
IL153592A0 (en)	2003-07-06
DE60103284D1 (de)	2004-06-17
ATE266421T1 (de)	2004-05-15
PT1309352E (pt)	2004-09-30
EP1309352A1 (de)	2003-05-14
GB2365770B (en)	2002-07-31
US7732450B2 (en)	2010-06-08
GB0020486D0 (en)	2000-10-11
US20040063722A1 (en)	2004-04-01
AU2001276567B2 (en)	2006-02-16

Legal Events

Date	Code	Title	Description
2006-06-28	EEER	Examination request
2012-08-14	MKLA	Lapsed

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